Hawaii Vacation Rentals – Island Condos, Beachfront Homes & Luxury Villas
Welcome to your guide for Hawaii vacation rentals, where tropical luxury meets everyday comfort. From sunrise-facing lanais on Maui to private bungalows near the lush valleys of Kauai, each rental is handpicked for quality, location, and local charm.
Why Book a Vacation Rental in Hawaii?
Unlike traditional hotels, vacation rentals provide full kitchens, private lanais, and dedicated living space—ideal for families, couples, or long stays. Many homes are steps from the beach, offer high-speed Wi-Fi, and include perks like pools, BBQ areas, or resort access.
Popular Vacation Rental Locations
- Waikiki, Oahu – High-rise condos near beaches, shops & nightlife
- Kihei, Maui – Walkable, affordable, and family-friendly
- Princeville, Kauai – Scenic cliffs, golf, and luxury condos
- Kailua-Kona, Big Island – Oceanfront escapes with sunset views
Rental Types Available
- Beachfront Condos with resort amenities
- Private Beach Homes with full kitchens
- Luxury Villas with pools & panoramic views
- Studios & Bungalows for solo travelers or couples
What Makes To-Hawaii.com Rentals Stand Out?
- Verified properties across all major Hawaiian islands
- Detailed descriptions, amenities, and photo galleries
- Helpful internal links to top Hawaii activities and Hawaii rental cars
- Flexible booking options, from weekend getaways to long-term stays
Plan Your Dream Island Escape
Explore the beauty of the islands with confidence. Whether you're whale watching on Maui, snorkeling on Oahu, or enjoying a peaceful sunrise on Lanai, our vacation rentals offer the perfect base for unforgettable memories. Start planning your Hawaiian adventure today.
OCEANFRONT Platinum Five Star remodeled villa! FRONT ROW!! Water views!! 27G1-2
This fabulous meticulously remodeled (recently) extra large one bedroom TWO bath villa (1300 square feet) is located within the Kapalua Bay Villa premier oceanfront complex. This villa, (significantly larger than ALL one bedroom level villas in the resort), is situated...
Spectacular Ocean View, Privacy, Sunsets & Whales from Lanai, Konea Tower #544
Spectacular OCEAN VIEW from our 5TH FLOOR KONEA extra large one bedroom one bath home #544 on the much preferred quiet and shady north side of the KONEA tower. Wake each morning to stunning ocean views from your king-size bed and spacious lanai. Floor to ceiling 'nana'...
LUXURY DIRECT OCEANFRONT! Fully Renovated! Free Parking! Sleeps 6
Waikiki Shore #700 – 2161 Kalia Rd.TRUE direct beachfront unit overlooking the sandy Waikiki shoreline with breathtaking panoramic ocean views! Gorgeously renovated from top to bottom in 2021 with FREE onsite Parking and everything you need for a luxurious Hawaiian...
🏖️Concierge Included | Ocean View | Walk to Beach! | Cental AC | vrKCV
vrKCV - Na Hale O Keauhou E6, Professionally Managed by Kona Coast VacationsEscape to paradise at Na Hale O Keauhou E6! Nestled in the serene and popular Na Hale O Keauhou complex, this townhome offers everything you need for a relaxing Hawaiian getaway. Just a short...
KBM Resorts | FREE CAR | Maui Kaanapali Villas | Renovated Studio Near Beach Central A/C! MKV-B-247
Newly renovated studio at Maui Kaanapali Villas with ocean views, vaulted ceilings, full kitchen, king bed, queen sofa sleeper, and lanai. Steps from the beach, perfect for a peaceful Maui retreat.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii...
Beautiful conveniently located 2-bedroom ocean view home in Kailua-Kona.
Beautiful and peaceful two bedroom home with an ocean view and convenient location. Located 7 minutes from the airport and 5 miles from town. Easy access to beaches, grocery stores, and everything Kona has to offer. This two bedroom space is the second floor of a...
Magnificent Mountain Views ~Near Beaches & Village
We've got everything you need to enjoy your holiday: bicycles, boogie boards, beach chairs, umbrellas, BBQ and many other amenities.Only a 15 minutes drive to Hanalei Bay, Hideaways and Aninni Beach and a short stroll to Queen's Bath plus the amenities of Princeville...
Upscale Kailua Getaway: Steps to Swim Beach!
An unforgettable Hawaiian escape awaits at this luxurious 3-bedroom, 2-bathroom Kailua vacation rental home! Sip your coffee on the deck, then walk to Lanikai Beach to enjoy the morning waves. Spend your days relaxing in the private pool, lounging in the hammock, or...
Luxury house in Mauna Kea & Hapuna Resort: Private Pool & Hot tub.
Aloha and welcome to your slice of paradise at Wai‘ula‘ula, nestled within the prestigious Mauna Kea Resort. This rare 4-bedroom private home showcases sweeping ocean views, a private infinity pool, and a separate Ohana cottage with its own entrance — offering the...
Mid-century Remodeled Spectacular Ocean Views! 10% Discount for Week+ Stays!
Our spacious remodeled vacation home has amazing ocean, Bali Hai and golf course views and now boasts updated modern bathrooms with Hans Grohe rain showers and fixtures plus a free-standing tub in the master bathroom, state of the art kitchen with Caesarstone counters...
Spectacular View Home for 20! Ocean, Mountain, golf views! 5min from Poipu beach
Brand new listing on VRBO; I'm a Super host for the past 3 years on Air B&BThis newly constructed luxury home sleeps 20+; it's perfection for multigenerational gatherings, vacationing with a few families or large groups. Partial ocean views sits backing the Kukui’ula...
Best Location @ Ekahi... year round sunsets from lanai, stroll to the Beach
What you will love about 14C: * CDC cleaning guidelines implemented * laundry done off site in professional grade CDC protocol machines* “Touchless” checkin * Expansive ocean view from multiple lanais* air conditioned, 3 flat panel tv's, fast internet, sonos...
Legendary Estate 50 Steps to Maui's Best Beach! New! 5 Bedroom, Pool with Slide!
Have you been dreaming about the ultimate Hawaii family vacation? Do you dream of a property that sits across the street from the top beach on Maui? Welcome to this incredible estateAs one of the only properties on Maui this close to an impeccable sandy beach, you'll...
Vintage Kahuna Waikoloa Beach Villas D1
Welcome to our Big Island Kahuna with a Touch of Nostalgia condo in Waikoloa! We are excited to have you as our guests. This beautifully appointed 3-bedroom, 3-bathroom townhome at Waikoloa Beach Villas offers both privacy and convenience. You'll love its close...
30-Day Stay at Kailua-Kona House w/ Hot Tub!
Breathtaking views, vibrant marine life, and screensaver-worthy beaches await when you visit this 2-bedroom, 2-bath home in Kailua-Kona. Once you've settled in, choose to relieve your post-travel stresses with a soak in the private hot tub or cocktails on the spacious...
Dream Vintage Surf Cottage TVNC 4301
Step back in time in this charming cottage by the beach. Built in the 1920's, this plantation style home will give you a true Hanalei experience. Just steps to the beach and a short stroll or bike ride to many restaurants and shopping. This is a dream location in the...
Hilton Pool Pass thru 2025. Golf Discounts. Waikoloa Beach Villas L2
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas L2Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: One Queen BedLiving Room: Sleeper SofaHilton Pool Pass: Valid for stays...
G & Z Upcountry Bed & Breakfast Cottage in Kula
G & Z Upcountry Bed & Breakfast Cottage, situated on half an acre in Kula Maui is adjacent to the hosts' 6-acre farm. TMK 2-2-2-006-101-0000.A large jacaranda and two avocado trees shade the wide-open lawn. At an elevation of around 3,000 feet, guests welcome the day as...
🏖️Spacious Townhome | Stunning Golf Course Views | vrKCV
vrKCV - Mauna Lani Village 407, Professionally Managed by Kona Coast VacationsLuxury Mauna Lani Villages Townhome – Golf Course Views & Exclusive Beach Club AccessEscape to paradise in this spacious, luxury townhome nestled within the exclusive gated community of...
Alii Cove#Q3 Beautiful ground floor spacious 2 bedroom with Ac
Alii Cove#Q-3 is an excellent beautifully furnished option for your Vacation. This spacious 2 bedroom, 2 bath unit has fantastic features that many guests enjoy. A perfect option for up to 6 people. ~No stairs! Beautiful Tile and new Laminate Flooring throughout the...
Fairways Ko Olina 27H: Your Ultimate 3BR Retreat in Hawaii with Resort Access
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Step into paradise with a stay at Fairways at...
Fabulous, Spacious Oceanview 3 Bedroom Condo with A/C!
Welcome to Ola Loa Hale!!! (Long Life House) This large three-bedroom, two-bathroom condo is the perfect choice for family and friends traveling together. The home is located in the beautiful Keauhou Kona Surf & Racquet Club, a gated resort community that has long been...
Upscale Oceanfront Penthouse Vistas
Summary:Full remodel and decorated in May 2023 with all new furnishings. This elegant 2-bedroom, 2-bath condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei at Menehune Shores resort, all of Maui is within reach. Beach chairs,...
Pili Mai 13B 4Bedroom AC POOL
Pili Mai 13B is your perfect Island home… With views of rolling greens and distant ocean views from the lanai and bedroom windows. While the entrancing Ha’upu Mountains greet you with Aloha. Pili Mai is an exclusive resort that provides a wonderful escape while...
Spacious Poolside Villa | Gourmet Kitchen, Lanai
Summary:D211 | TA-018-220-0320-02Welcome to your tropical retreat in sunny Poipu! Villa D211 is a luxurious 3-bedroom, 3-bathroom poolside villa offering 1,600 sq ft of thoughtfully designed indoor-outdoor living. Ideal for families or groups, this elegant space blends...
Contemporary Hawaii Living, Calm North Shore Beach
Experience Hawaii in its purest form in this beautifully built custom home, sitting on an exclusive beachfront property on the North Shore of Oahu. Built with the idea of taking in the gorgeous ocean and mountain views, and maximizing the flow of the trade winds, this...
Amazing condo with pools and hotub across from the beach
Welcome to Maui Kamaole! This wonderful 1 Bed/2 Bath condo is the perfect location for your Maui vacation. It is conveniently located across the street from the Kamole Beach Parks and is nearby shops and restaurants. This updated, fully equipped kitchen makes it perfect...
Very spacious for a one bedroom condo and completely set up with brand new furnishings!
This Hawaiian vacation condo has been beautifully upgraded with stone flooring, dark wood cabinets and granite counter tops throughout.You'll love the ease of a walk in ground level unit with no stairs.An open floor plan leads from kitchen to dining to the sunken living...
Pomaika'i : New Poipu Villa w/Pool+Spa Near Beach
This lovely, spacious South Shore home is the epitome of a laid-back vacation villa: located on the 18th fairway of the Kiahuna Golf Course, splashed with sunlight, canopied by blue skies, surrounded by tropical greenery. With its shimmering turquoise pool and whirlpool...
Location! 2br/1ba Condo 2 blocks to Waikiki main beach, on-site parking
Beautifully decorated Waikiki 2br/1ba 8th floor condo in secured building, pool, assigned parking, steps to public transportation, a/c, in unit washer/dryer, new mattresses (Master bedroom king mattress, second bedroom queen mattress), new paint and new flooring, 2...
Sunset Suzy's tropical retreat! One free night! After 7 nights.
Sunset Suzys Tropical Retreat is located perfectly 15 minutes outside of Hilo town in a beautiful neighborhood called Hawaiian Paradise park.. It is located on a beautiful one acre lot, filled with fruit trees, green grass, green geckos, and tropical birds. There are no...
Bed and Breakfast on the Slopes of Haleakala
Enjoy bed and breakfast on the mountain in a tranquil contemporary designed guest-suite with private entrance and patio garden in a friendly and local neighborhood where a unique experience awaits you on the slopes of Maui’s Haleakala Mountain.Within walking distance...
North Shore Oasis: Tropical Waterfall Garden & Bali Hai Sunsets
Welcome to the North Shore Oasis! Like the nicest hotels, the Oasis has a magical indoor/outdoor Hawaiian vibe. The open-air home let's you live among the tropical breeze. For your comfort, all three bedrooms have A/C.The Oasis is located on the 11th green of the Makai...
OCEANFRONT TWO BEDROOM CONDO with A/C! Cal King Beds in Both Bedrooms!
Imagine - Warm tropical climate, sounds of waves washing ashore, palm trees swaying in the breeze, panoramic views, and the perfect accommodations - is there any other way to experience Hawaii?? This two bedroom, two-bath condo gives you all of that and more! The very...
Home Brought Back to Life Hidden Off One of Hilo's Main Streets.
Aloha! We are Keone and Yonnell Farias. We were both born and raised here on this wonderful island. We welcome you to our beautiful re-done home and would be happy to share with you our favorite places. Located in a quiet neighborhood of Waiakea Uka, we are a short...
❤️PiH❤️ Sun Cottage ★ Private Detached ★ Close to Pools & Fitness ★ Bikes
Brought to you by Paradise in Hawaii Luxury Homes.Sun Cottage is a wonderful 3 bedroom/3 bathroom detached home that offers everything that you would ever desire on your Big Island vacation in Mauna Lani. Sun Cottage is a single-story, free-standing home (no stairs and...
Elegant suite with a large lanai and ocean views
Step into Kaanapali Shores 401, a spacious 2-bedroom, 2-bathroom condo that offers central A/C, a private washer/dryer, and panoramic ocean views. This property has elevators. Unit 401 can comfortably accommodate up to 6 guests. The master bedroom boasts a king-sized...
My Perfect Stays: New Listing Special
Maui Eldorado E106 is a studio condo that comfortably accommodates up to four guests, featuring a king bed and a queen sofa bed. Enjoy lush garden views and just 5 steps to a small pool—perfect for a relaxing island getaway.Savor your meals al fresco on the...
Pohailani #113 - Vacation West Maui - Gorgeous Studio with AC
This studio is perfect for travelers who want to be close to the ocean and enjoy all the amenities of a vacation rental. Just a short walk from local restaurants and coffee shops, making it easy to grab a bite to eat or a coffee on the go. This property features on-site...
Maui Banyan king, 2 bathroom, steps to Kamaole beach, sleeps 4 - No parking fee
In Maui its all about LOCATION and this unit is in the perfect spot. Maui Banyan is located in prime South Kihei where the weather is sunny and beautiful year round. It’s across the street from Kamaole Beach II which is one of the few beaches in Maui with a lifeguard...
🏖️Waikoloa Gold Member Golf Discounts | Spectacular Ocean Views | vrKCV
vrKCV - Hali'i Kai 12F, Professionally Managed by Kona Coast VacationsSpectacular Ocean Views and Exclusive Golf PrivilegesWelcome to Hali'i Kai 12F, where breathtaking views and luxurious amenities come together to create the ultimate Hawaiian retreat. Situated along...
NEW Gorgeous BEACHFRONT Condo with Fabulous Ocean Views! Fully Renovated!
Waikiki Shore #702 – 2161 Kalia Rd.NEW TO OUR INVENTORY and FULLY RENOVATED! This condo is perfect for 2 couples or up to 6 guests (STRICT MAX OCCUPANCY, using optional rollaway beds).– Contemporary beachfront condo overlooking famous Waikiki Beach with spectacular...
Executive Gold Coast Oceanfront Suite: Diamond Head Views, Amazing Seaside Pool
Executive Gold Coast Oceanfront Suite offers refined island living with nearly 360-degree views of Waikiki’s Gold Coast, Diamond Head, and the blue Pacific. This two-bedroom, two-bathroom retreat at Coral Strand blends tropical elegance, modern convenience, and an...
Sky Villa Estate: Luxury Gated Kona Retreat with Ocean Views
Welcome to your Hawaiian haven, Sky Villa Estate! Kick off your flip-flops and let alohaspirit guide you up the driveway to this secluded gated 5-acre estate, through lushlandscape that feels like a warm hug from the island itself. Deep lush lawns encouragefamily games...
Wailea Ekahi 54A: Completely Remodeled & Panoramic Ocean View
Our Family has Two - Two Bedroom/Two Bathroom Units above and Below Each other in Ekahi Village. This is great for Families or large groups traveling together. Both units tend to be among the most popular in the entire complex! VIEWS: Ocean views from nearly every...
Kona Isle B34 - Ocean View, Top Floor with full AC. Peaceful Oceanfront Complex.
2025 REDUCED SUMMER RATES!NEW: In an effort to provide you with outstanding accommodations, we have upgraded to a dual-air conditioning unit that allows for whole-unit AC. We've also upgraded to quartz countertops! Aloha from Hale Malina! We invite you to enjoy a little...
Charming 1-bedroom apartment in Waikiki. 1 block from the beach
Unwind in Honolulu at this amazing apartment. This cool space features 1 bedroom with a king bed, a cozy living room with an extra twin bed, and a modern bathroom with a shower. Guests can enjoy amenities like WiFi, AC, and a washing machine during their stay....
Waiulu Estate Villa - Waiulu Golf & Oceanview Estate Hualalai
Welcome to the exquisite Waiulu Estate Villa at Four Seasons Hualalai Resort. This estate offers a private and serene setting with close wide-open ocean views. The estate has been recently updated with new contemporary décor by the renowned Henderson Design Group....
Panoramic Ocean View 1BR Condo Suite 150 feet from the Ocean at Papakea Ocean Front Resort by RedAwning
Welcome to our fully remodeled and fully furnished One bedroom condo suitewith stunning panoramic ocean view at Ocean Front Papakea resort, less thantwo minutes from the beach. This condo suite is tastefully furnished and hasCalifornia King Bed, full kitchen (not a...
Kai Lani Luxurious Ocean View Gated Community, Two Master Bedrooms near Aulani
Please visit our exceptional vacation condo in the Kai Lani gated community, a part of the beautiful Ko’olina resort. Our ground floor luxury, executive-type condo is over 1300 Sq. ft. with a full ocean view from our lanai where you can sit at night viewing the sun...